ipso Nitration. XXIX. Nitration of substituted 4-methylanisoles and phenols

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Abstract
Nitration of 2-chloro-4-methylanisole (1a) in acetic anhydride gives (Z)-4-chloro-3-methoxy-6-methyl-6-nitrocyclohexa-2,4-dienyl acetate (2a), 2-chloro-4-methyl-4-nitrocyclohexa-2,5-dienone (3a), and 2-chloro-4-methyl-6-nitroanisole (4a). Similarly 2-bromo-4-methylanisole (1b) gives (Z)-4-bromo-3-methoxy-6-methyl-6-nitrocyclohexa-2,4-dienyl acetate (2b), 2-bromo-4-methyl-4-nitrocyclohexa-2,5-dienone (3b), and 2-bromo-4-methyl-6-nitroanisole (4b), whereas 4-methyl-2-nitroanisole (1c) gives (Z)-3-methoxy-6-methyl-4,6-dinitrocyclohexa-2,4-dienyl acetate (2c), (Z)-3-methoxy-6-methyl-2,6-dinitrocyclohexa-2,4-dienyl acetate (7), and 4-methyl-2,6-dinitroanisole (4c). Nitration of 3-chloro-4-methylanisole (9a) gives 3-chloro-4-methyl-4-nitrocyclohexa-2,5-dienone (10a), 3-chloro-4-methyl-2-nitro anisole (11a), and 5-chloro-4-methyl-2-nitroanisole (12a), and 4-methyl-3-nitroanisole (9c) gives (Z)-3-methoxy-6-methyl-5,6-dinitrocyclohexa-2,4-dienyl acetate (13), 4-methyl-2,3-dinitroanisole (11c), and 4-methyl-2,5-dinitroanisole (12c). Nitration of 2-chloro-4-methylphenol (14) in chloroform gives 3a and 2-chloro-4-methyl-6-nitrophenol (5a), and 3-chloro-4-methylphenol (15) gives dienone 10a, 3-chloro-4-methyl-2-nitrophenol (16), and 5-chloro-4-methyl-2-nitrophenol (17).

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